What does a Jolly Roger flag usually depict?
And the answer: a skull and crossbones.
During the 18th century, the Jolly Roger was the English name for the flags flown to identify a pirate ship about to attack. Today we know the design as a white skull and crossbones, on a black background.
The term "Jolly Roger" was first used by Charles Johnson in 1724, in a book titled A General History of the Pirates. In it, Johnson draws the term from two pirate captains themselves, who used the term to refer to their own ships. Interestingly, because neither captain's flag actually donned the classically associated skull and crossbones, Jolly Roger was likely a term that had been commonly used amongst pirates in reference to the simple black flag of piracy.
The term "Old Roger," meanwhile, was a term that the British used to refer to the devil, and was often depicted on a black flag. Any ship whose sails flew such a flag was to indicate that the signified dead was approaching, and would show mercy if the crew surrendered. However, if a red flag was flown, it was to indicate that the pirates would show no mercy (i.e., you better hightail it out of there).
Most of the time, pirates didn't proudly fly the pirate flag. Instead, they would masquerade themselves with Spanish, French or Dutch colors until they were in range of their intended target. In time, the flag became a calling card for pirates, inspiring fear overseas.
Learn more about the history of the Jolly Roger flag below.